DE10136449A1 - Substituted aryl ketones - Google Patents

Abstract

The invention relates to novel arylketones of formula (I) wherein A<1>, A<2>, Q, R<1>, R<2>, X, Y and Z have the meaning cited in the description, the use thereof as herbicides and to methods and intermediate products for the production thereof.

Description

The invention relates to new substituted aryl ketones, processes for their preparation and their use as plant treatment agents, in particular as herbicides.

It is already known that certain substituted aryl ketones have herbicidal properties have properties (cf. EP-A-090 262, EP-A-135 191, EP-A-186 118, EP-A- 186 119, EP-A-186 120, EP-A-319 075, EP-A-352 543, EP-A-418 175, EP-A- 487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP-A-609 797, EP-A- 609 798, EP-A-625 505, EP-A-625 508, EP-A-636 622, US-A-5 804 532, US-A- 5 834 402, US-A-5 846 906, US-A-5 863 865, WO-A-95/31466, WO-A-96/26192, WO-A-96/26193, WO-A-96/26200, WO-A-96/26206, WO-A-97/27187, WO-A- 97/35850, WO-A-97/41105, WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/43270, WO-A-97/46530, WO-A-98/28981, WO-A-98/31681, WO-A- 98/31682, WO-A-99/03856, WO-A-99/07688, WO-A-99/07697, WO-A-99/10327, WO-A-99/10328, WO-A-00/05221 and especially WO-A-00/21924). The effect however, these connections are not satisfactory in all respects.

The new substituted aryl ketones of the formula (I)

in which
A ^{1 represents} a single bond or O (oxygen),
A ^{2 represents} alkanediyl (alkylene), alkenediyl or alkindiyl,
Q represents O (oxygen) or S (sulfur),
R ^{1 stands} for hydrogen or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or for the grouping -C (Q) -R ² ,
R ² for hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, or for optionally substituted alkyl, alkyl carbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, dialkylamino, alkoxyamino, N-alkylalkoxyamino, alkylhydrazino, dialkylhydrazino, alkenyl, alkenyloxy , alkenylamino, Alkenyloxyamino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkyl alkyl, cycloalkylalkoxy, Cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, aryl, alkoxy, arylalkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy , Heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino,
X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or represents optionally substituted alkyl, alkoxy, alkyl thio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkyl aminosulfonyl,
Y stands for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally optionally substituted alkyl, alkoxy, alkyl thio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkyl aminosulfonyl, and
Z represents one of the groupings below

in which
m represents the numbers 0 to 6,
R ^{3 represents} hydrogen, halogen or optionally substituted alkyl, alkylthio or aryl, or - if m represents 2 - optionally also together with a second radical R ^{3 represents} oxygen or alkanediyl (alkylene),
R ⁴ for hydroxy, formyloxy, halogen, or for each optionally substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkyl carbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkyl sulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, aryl sulfmyl, arylsulfonyl, arylcarbonyloxy, arylcarbonyloxy, arylcarbonyloxy, sulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl,
R ^{5 stands} for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl,
R ^{6 stands} for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R ^{7 represents} hydroxyl, formyloxy, or optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylamino carbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy,
R ^{8 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl,
R ^{9 represents} hydrogen or represents optionally substituted alkyl or cycloalkyl,
R ^{10 represents} hydrogen or represents optionally substituted alkyl or cycloalkyl, and
R ^{11 represents} hydrogen, cyano, carbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl,
found.

The radical X is preferably at position (2) of the phenyl ring.

In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl - also in connection with heteroatoms, such as in alkoxy - in each case straight-chain or ver branches.

As far as the compounds of general formula (I) in different stereoiso meren forms may exist, the invention includes the respectively possible stereoisomeric forms.  

Preferred substituents or preferred ranges of the radicals present in the formulas listed above and below are defined below.
A 'preferably represents O (oxygen).
A ² preferably represents alkanediyl (alkylene), alkenediyl or alkindiyl, each having up to 6 carbon atoms.
Q is preferably O (oxygen).
R ¹ preferably represents hydrogen, in each case optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl alkyl, alkoxy , Alkylthio, alkylsulfinyl, alkyl sulfonyl or alkylamino each having 1 to 6 carbon atoms in the alkyl groups, for dialkylamino each having 1 to 4 carbon atoms in the alkyl groups, for alkenyl or alkynyl each optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms, for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl, for in each case optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the A. ryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for the grouping -C (Q) -R ² .
R ² preferably represents hydrogen, amino, cyanoamino, nitroamino, hydroxy amino, hydrazino, C ₁ -C ₄ -alkylcarbonyl, C ₁ -C ₄ -alkoxy-carbonyl, each optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl thio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylamino, alkoxyamino or alkylhydrazino, each having 1 to 6 carbon atoms in the Alkyl groups, for dialkylamino, N-alkylalkoxyamino or dialkylhydrazino, each having 1 to 4 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy or alkynylamino each having 2 to 6 carbon atoms each substituted by halogen for cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkylg, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - Halogenalkoxy or C ₁ -C ₄ - alkoxy-carbonyl substituted aryl, arylcarbonyl, aryloxy, aryloxy carbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylamino each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ -Alkylthio, C ₁ -C ₄ -haloalkylthio or C ₁ -C ₄ -alkoxy-carbonyl substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylalkyl, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heteriolcylyl heterocyllyl alkylcylyl cyclyl cyclyl alkyl, to 10 Ko Hydrogen atoms and additionally at least one heteroatom selected from the series nitrogen (N) (but not more than 5 N atoms), oxygen (O) (but not more than 2 O atoms), sulfur (S) (but not more than 2 S atoms), SO or SO ₂ and optionally additionally a group selected from oxo (C = O), thioxo (C = S), imino (C = NH), cyanoimino (C = N-CN), nitroimino (C = N-NO ₂ ) ,
X preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, or each optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - Alkylsulfinyl or C ₁ -C ₄ alkyl sulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups.
Y preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, or each optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - Alkylsulfinyl or C ₁ -C ₄ alkyl sulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups.
Z preferably represents one of the groupings below

m preferably represents the numbers 0 to 3.
R ³ preferably represents hydrogen, halogen, each alkyl optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl or alkylthio each having 1 to 6 carbon atoms, or for phenyl, or - if m is 2 - optionally together with a second radical R ³ for oxygen or alkanediyl (alkylene) with 3 to 5 carbon atoms.
R ⁴ preferably represents hydroxy, formyloxy, halogen, in each case optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy, each having 1 to 6 carbon atoms, for each optionally substituted by halogen, alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, for each optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ - haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ haloalkylsulfonyl substituted aryloxy, arylthio, arylsulfinyl, aryl sulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, aryl alkoxy, aryl , Arylalkylsulfinyl or arylalkylsulfonyl each with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
R ⁵ preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, in each case optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ - C ₄ alkylsulfonyl substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups or for cycloalkyl having 3 to 6 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl.

R ⁶ preferably represents hydrogen, optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkyl sulfonyl substituted alkyl with 1 up to 6 carbon atoms, for each optionally substituted by cyano or halogen alkenyl or alkynyl each having 3 to 6 carbon atoms, for each optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl cycloalkyl or cycloalkyl alkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each where appropriate by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl thio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ -Halogenalkylsulfonyl substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
R ⁷ preferably represents hydroxy, formyloxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, for each optionally by cyano or halogen substituted alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, or for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ - C ₄ - haloalkylsulfonyl substituted arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part.
R ⁸ preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkyl thio, alkylsulfinyl or alkylsulfonyl, each with 1 to in each case optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy 6 carbon atoms in the alkyl groups.
R ⁹ preferably represents hydrogen, alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl.
R ¹⁰ preferably represents hydrogen, alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, or cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl.
R ¹¹ preferably represents hydrogen, cyano, carbamoyl, halogen, or alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl, each of which has 1 to 6 carbon atoms in the alkyl groups and is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy ,
A ² particularly preferably represents methylene (-CH ₂ -), ethane-1,1-diyl (-CH (CH ₃ ) -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane -1,1-diyl (-CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (-CH ₂ CH ₂ CH ₂ -), butane-1,3-diyl (-CH (CH ₃ ) CH ₂ CH ₂ -), butane-1,4-diyl (-CH ₂ CH ₂ CH ₂ CH ₂ -), ethylenediyl, propendiyl, Butenediyl, ethindiyl, propindiyl or butynediyl.
R ¹ particularly preferably represents hydrogen, in each case optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i - Propylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i Propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethyl amino, n- or i-propylamino, n-, i-, s- or t-butylamino, for dimethyl amino or diethylamino, each optionally substituted by fluorine, chlorine and / or bromine Ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, each for cyclopropyl, cyclob, optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or propyl utyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy or trifluoromethoxy substituted phenyl, naphthyl, phenyl methyl, phenylethyl, naphthylmethyl or naphthylethyl or for grouping -C (Q) -R ² .

R ² particularly preferably represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, Methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methyl sulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t -Pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio , Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methoxyamino, ethoxyamino, n- or i-propoxy amino, n-, i-, s- or t-butoxyamino, Methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, for dimethylamino, diethylamino, N-methyl-methoxyamino, dimethylhydrazino or diethyl hydrazino, each optionally with fluorine, chlorine and / or Bromine substituted Ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, pentynyl, propenyloxy, butenyloxy, pentenyloxy, propenylthio, butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino, propenyloxy amino, butenyloxyamino, ethynyl, pentynyloxyamino, pentenyloxyamino, pentenyloxyamino , Butynyloxy, pentynyloxy, propynylamino, butynylamino or pentynylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or propyl, Cyclobutylamino, cyclo pentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutyl methoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethyl amino, cyclobuylmethylamino, cyclo or methylamino, cyclamethylamino, cyclamylamino, cyclopentylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclopentylmethylamino, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, Phenylcarbonyl, phenoxycarbonyl, phenylthio, phenylhydrazino, naphthyl, naphthylthio, naphthylamino, phenylethyl, phenylmethylthio, phenylmethylthio , or for any given case by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s - or t-butylthio, Difluor met hylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i- propoxycarbonyl substituted monocyclic or bicyclic hetero cyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylalkyl, hetero cyclylalkoxy or heterocyclylalkylamino, methyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, furyl, methylyl, methylyl, methylyl, methylyl, methylyl, methylyl, furyl Pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolyl methyl, imidazolyl, imidazolylmethyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, dihydrooxololazolyl (dihydrooxoloxazolyl), dihydrooxoloxazolyl , Tetrahydroisoxazolyl (Isoxazolidinyl), Oxazolylmethyl, Thiazolyl, Dihydrothiazolyl (Thiazolinyl), Tetrahydrothiazolyl (Thiazolidinyl), Thiazolylmethyl, Thiazolidinyl, Oxothiazolidinyl, Cyanoiminothiazolidinyl, Oxotriazolinyl, Oxidiazidinyl, Oxidethylamino-Diperidino-Vinylopyridino-Vinylophenyl 2-oxo-1-aza-cyclo heptyl, 2-oxo-1,3-diaza-cycloheptyl, morpholinyl, morpholinylamino, piper azinyl, pyridinyl, pyridinyloxy, pyridinylamino, pyridinylmethyl, pyridinyl methoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl, pyrimidinyl methoxy.
X particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or, if appropriate, in each case by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethyl thio, methylsulfinyl, ethylsulfinyl, Methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t -Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl sulfonyl, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.
Y particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or, if appropriate, in each case by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, Methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t -Butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl sulfonyl, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.
m particularly preferably represents the numbers 0, 1 or 2.
R ³ particularly preferably represents hydrogen, fluorine, chlorine or bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl , Methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-Butylthio, or for phenyl, or - if m is 2 - optionally together with a second radical R ³ for oxygen, propane-1,3-diyl or butane-1,4-diyl.
R ⁴ particularly preferably represents hydroxyl, formyloxy, fluorine or chlorine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfinyl , Methylsulfonyl or ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyl Ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyl oxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propenyloxy, butyloxy, optionally substituted by fluorine, chlorine and / or bromine, respectively or butynyloxy, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, phenifylphenyl, phenylylphenyl, phenylylphenyl, phenyl, methylphenyl, phenyl, methylphenyl, phenyl, methylphenyl, phenyl, methylphenyl, phenyl, Phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl.
R ⁵ particularly preferably represents hydrogen, cyano, carbamoyl, thio carbamoyl, fluorine, chlorine or bromine, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio , n- or i-Propyl thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for cyclo propyl, cyclobutyl, which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, Cyclopentyl or cyclohexyl.
R ⁶ particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl thio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butynyl which is optionally substituted by cyano, fluorine, chlorine or bromine, if appropriate by in each case by Cyano, fluorine, chlorine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i- Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s - or t-butylthio-methylthio, ethyl thio, n- or i-propylth io, difluoromethylthio, trifluoromethylthio, methyl sulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenyl or phenylmethyl.
R ⁷ particularly preferably represents hydroxyl, formyloxy, for methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each optionally substituted by cyano, fluorine, chlorine Propenyloxy, butenyloxy, propynyloxy or butynyloxy, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy , Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethyl ylsulfonyl substituted phenyl methoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyl oxy.
R ⁸ particularly preferably stands for hydrogen, cyano, carbamoyl, thio carbamoyl, fluorine, chlorine or bromine, or for methyl, ethyl, n- or substituted in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
R ⁹ particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, or for cyclo propyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally substituted by cyano, fluorine, chlorine, methyl or ethyl.
R ¹⁰ particularly preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, or for cyclo propyl, cyclobutyl, cyclopentyl or cyclohexyl, optionally substituted by cyano, fluorine, chlorine, methyl or ethyl.
R ¹¹ particularly preferably represents hydrogen, cyano, carbamoyl, fluorine, chlorine or bromine, or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, Ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
A ² very particularly preferably represents methylene (-CH ₂ -), ethane-1,2-diyl (di methylene, -CH ₂ CH ₂ -) or propane-1,3-diyl (-CH ₂ CH ₂ CH ₂ - ).
R ¹ very particularly preferably represents hydrogen, in each case optionally methyl, ethyl, n- or i-propyl, n- or substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl i-butyl, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethyl amino, n- or i-propylamino, for dimethylamino, each optionally with fluorine and / or Chlorine-substituted propenyl, butenyl, ethynyl, propynyl or butynyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, optionally substituted by cyano, fluorine, chlorine or methyl, or for each optionally by nitro, cyano, Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted Phenyl, phenylmethyl or phenylethyl, or for grouping -C (Q) -R ² .
R ² very particularly preferably represents hydrogen, amino, hydroxyamino, hydrazino, in each case optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl , Methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- Propylthio, methylamino, ethylamino, n- or i-propylamino, methoxyamino, ethoxy amino, n- or i-propoxyamino, for dimethylamino, for N-methyl-methoxy amino, for dimethylhydrazino, for each optionally substituted by fluorine and / or chlorine ethenyl , Propenyl, butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, each for cyclopropyl, cyclobutyl, cyclopentyl, cyclobentyl, optionally substituted by cyano, fluorine, chlorine or methyl clohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexyl methyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylamino, phenylmethyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine , Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, Trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, furylmethyl, furylmethyl , Thienylmethyl, pyrrolidinyl, oxo pyrrolidinyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, imidazolyl, imidazolylmethyl, 2-oxo-1,3-diazacyclopentyl, oxazolyl, isoxazolyl, oxazolylmethyl, isoxazolidyl, oxidolylidylylidylylipyrylolylylipyrylolylylipyrylolylylipyridylylipyridylylipyridylylpyridylmoprolyl 1,3-diazacyclohexyl, morpholinyl, piperazinyl, pyridinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl.
X very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methyl sulfinylmethyl, methylsulfonylmethyl, methoxy, Ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
Y very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methyl , Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
m very particularly preferably represents the numbers 0 or 1.
R ³ very particularly preferably represents hydrogen, in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or phenyl, or - for the case that m is 2 - optionally together with a second radical R ³ for oxygen, propane-1,3-diyl or butane-1,4-diyl.
R ⁴ very particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, which are each optionally substituted by fluorine and / or chlorine , Ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonylyloxy, for optionally propenyloxy, butenyloxy, propynyloxy or butynyloxy substituted by fluorine and / or chlorine, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy or trifluoromethoxy substituted phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethox y, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl.
R ⁵ very particularly preferably represents hydrogen, cyano, fluorine, chlorine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, each optionally substituted by fluorine and / or chlorine , n- or i-Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for cyclopropyl optionally substituted in each case by cyano, fluorine, chlorine or methyl.
R ⁶ very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, each in each case optionally propenyl, butenyl, propynyl or butynyl substituted by fluorine or chlorine, each for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine or methyl, or for each optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-Propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or phenylmethyl.
R ⁷ very particularly preferably represents hydroxyl, formyloxy, methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy - or i-Butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, each optionally substituted by fluorine and / or chlorine , Butenyloxy, propynyloxy or butynyloxy, or for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy Phenyl methoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenylsulfonyl oxy.
R ⁸ very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy. Butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propyl thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
R ⁹ very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
R ¹⁰ very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or cyclopropyl optionally substituted by fluorine, chlorine or methyl.
R ¹¹ very particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-, each optionally substituted by fluorine, chlorine, methoxy or ethoxy. Propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl.
R ¹ most preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, methoxy or ethoxy or the group -C (Q) -R ² .
R ² most preferably represents hydrogen, amino, hydrazino, each methyl, ethyl or n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, methylamino, ethylamino, n- or i-propylamino or dimethylamino, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine or methyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl or n- or i-propyl, methoxy, ethoxy or n- or i- Propoxy substituted phenyl, phenylamino, phenylmethyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, methyl thio , Ethylthio, difluoromethylthio, trifluoromethylthio, methoxycarbonyl or ethoxycarbonyl substituted furyl, furylmethyl, thienyl, thienylmethyl, pyrrolyl or pyrrolylmethyl.
X most preferably represents hydrogen, nitro, fluorine, chlorine, bromine, methyl, ethyl or trifluoromethyl.
Y most preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, methylthifluoromethoxy , Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.
R ³ most preferably represents hydrogen or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine.
R ⁴ most preferably represents hydroxy.
R ⁵ most preferably represents hydrogen, fluorine, chlorine or, where appropriate, substituted by fluorine and / or chlorine, methyl, ethyl, methoxy or ethoxy.
R ⁶ most preferably represents hydrogen or methyl, ethyl, n- or i-propyl or n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.
R ⁷ most preferably represents hydroxy, methoxy or ethoxy optionally substituted by fluorine or chlorine, or phenylmethoxy optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy or ethoxy.

According to the invention, preference is given to the compounds of the formula (I) in which one A combination of the meanings listed above as preferred is present.

According to the invention, particular preference is given to the compounds of the formula (I), in which a combination of the Be listed as particularly preferred above interpretations are available.

According to the invention, very particular preference is given to the compounds of the formula (I), in which are a combination of those listed above as being particularly preferred Meanings exist.  

Most preferred according to the invention are the compounds of formula (I), in which is a combination of those listed as most preferred above Meanings exist.

The compounds of the formulas (I-1) to (I-3) are particularly emphasized:

A ¹ , A ² , Q, R ¹ , R ² , X, Y and Z each have the meanings given above as preferred or very particularly preferred.

The compounds of the general formulas (I-2A) to (I-2D) are particularly emphasized:

m, A ¹ , A ² , Q, R, R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , X and Y each have the above as preferred or very particularly preferred meanings.

Of the compounds of the formulas (I-1) to (I-3) and (I-2A) to (I-2D), those in which A ^{1 stands} for a single bond and A ² stands for methylene should be particularly emphasized ,

The compounds of the formulas (I-1) to (I-3) and (I-2A) to (I-2D) are also those in which A ^{1 is} O (oxygen) and A ^{2 is} ethane-1 , 2-diyl (dimethylene) is particularly highlighted.

The general or priority areas listed above Definitions apply both to the end products of formula (I) and accordingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.

The new substituted aryl ketones of formula (I) are characterized by strong and selective herbicidal activity.

The new substituted aryl ketones of the formula (I) are obtained if

• a) Amino compounds of the general formula (II)
  in which
  A ¹ , A ² , R ¹ , X, Y and Z have the meaning given above,
  with compounds of the general formula (III)
  in which
  Q and R ^{2 have} the meaning given above and
  Q ^{1 represents} halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or phenylthio,
  - or, if appropriate, with corresponding iso (thio) cyanates -
  optionally in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents, or if one
• b) carboxylic acids of the general formula (IV)
  in which
  A ¹ , A ² , Q, R ¹ , R ² , X and Y have the meaning given above
  - or reactive derivatives thereof, such as. B. corresponding acid halides, acid cyanides or esters -
  with compounds of the general formula (V)
  HZ (V)
  in which
  Z has the meaning given above,
  if appropriate in the presence of a dehydrating agent and if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
  or if you
• c) substituted benzoyl ketones of the general formula (Ia)
  in which
  A ¹ , A ² , Q, R <; S 56894 00070 552 001000280000000200012000285915678300040 0002010136449 00004 56775UP <1, R ² , R ¹⁰ , X and Y have the meaning given above,
  with an orthoformic acid ester or with an N, N-dimethyl-formamide acetal or with a cyanoformic acid ester or with carbon disulfide (carbon disulfide) and an alkylating agent and then with hydroxylamine or an acid adduct thereof
  if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
  or if (d) aryl ketones of the general formula (VI)
  in which
  A ¹ , A ² , Q, R ¹ , X, Y and Z have the meaning given above and
  Q ^{2 represents} halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or phenylthio,
  - or, if appropriate, corresponding iso (thio) cyanates -
  with compounds of the general formula (VII)
  HR ² (VII)
  in which
  R ^{2 has} the meaning given above,
  if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
  and, if appropriate, after carrying out the processes (a), (b), (c) or (d) according to the invention on the compounds of the general formula (I) thus obtained as part of the definition of substituents, subsequent reactions (for example substitution, oxidation, or reduction reactions) for conversion into other compounds of the general formula (I) by conventional methods.

If, for example, [3- (2-amino-ethoxy) -2-chloro-4-methylthiophenyl) - (5-ethyl-4-isoxazolyl) methanone and propionic acid chloride are used as starting materials, the course of the reaction in the process according to the invention (a ) are outlined by the following formula scheme:

If, for example, 4-bromo-3 - [[(1-pyrrolidinylthioxomethyl) amino) methyl] benzoic acid and cyclohexane-1,3-dione are used as starting materials, the reaction sequence in process (b) according to the invention can be carried out using the following formula scheme are outlined:

For example, if one uses N- [2-chloro-5- (3-cyclopropyl-3-oxo-propanoyl) - benzyl] -acetamide, N, N-dimethyl-formamide-diethylacetal and hydroxylamine as Starting materials, the course of the reaction in process (c) according to the invention can be outlined by the following formula:  

If, for example, N - [[2-bromo-5 - [(5-hydroxy-1-methyl-1H-pyrazol-4-yl) carbonyl] phenyl] methyl] carbamic acid O-methyl ester and pyrrolidine are used as the starting material materials, the course of the reaction in process (d) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the amino compounds to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), A ¹ , A ² , R ¹ , X, Y and Z preferably have those meanings which are preferred, particularly preferred, in connection with the description of the compounds of the general formula (I) according to the invention, very particularly preferably or most preferably for A ¹ , A ² , R ¹ _, X, Y and Z have been given.

The starting materials of the general formula (II) are not yet from the literature known; as new substances, they are also the subject of the present application.  

The new amino compounds of the general formula (II) are obtained if halogen compounds of the general formula (VIII)

in which
A ¹ , A ² , X, Y and Z have the meaning given above and
X ^{1 represents} halogen (preferably fluorine, chlorine, bromine or iodine, in particular chlorine or bromine),
with ammonia or amino compounds of the general formula (IX)

in which
R ^{1 has} the meaning given above,
optionally in the presence of a diluent, such as. B. tetrahydrofuran, optionally under elevated pressure at temperatures between 0 ° C and 100 ° C (see. The preparation examples).

The precursors of the general formula (VIII) are known and / or can processes known per se (cf. WO-A-95/31446, WO-A- 00/68227, production examples).  

The precursors of the general formula (IX) are known synthetic chemicals.

Formula (III) provides a general definition of the (thi) oxo compounds to be used as starting materials in process (a) according to the invention for the preparation of compounds of the general formula (I). In the general formula (III), Q and R ³ preferably have those meanings which are preferred above, particularly preferred, very particularly preferred for Q and in connection with the description of the compounds of the general formula (I) according to the invention R ^{3 have been} given; Q ¹ preferably represents fluorine, chlorine, bromine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the general formula (III) are known organic synthesis chemicals.

Formula (IV) provides a general definition of the carboxylic acids to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I). In the general formula (IV), A ¹ , A ² , Q, R ¹ , R ² , X and Y preferably have those meanings which are preferred above in connection with the description of the compounds of the general formula (I) according to the invention, particularly preferred, very particularly preferred or most preferred for A ¹ , A ² , Q, R ¹ , R ² , X and Y have been given.

The starting materials of the general formula (IV) are not yet from the literature known; as new substances, they are also the subject of the present application.

The new carboxylic acids of the general formula (IV) are obtained if
(α) iso (thio) cyanates of the general formula (X)

in which
A ¹ , A ² , Q, X and Y have the meaning given above and
R represents hydrogen, an alkali metal or alkaline earth metal equivalent (preferably a sodium or potassium), or alkyl (preferably C ₁ -C ₄ alkyl, especially methyl or ethyl),
with compounds of the general formula (VII)

HR ² (VII)

in which
R ^{2 has} the meaning given above,
optionally in the presence of a diluent, such as. B. acetonitrile or ethanol, at temperatures between 0 ° C and 100 ° C and, if appropriate, subsequently carries out ester hydrolysis by customary methods (cf. the preparation examples),
or if you
(β) amino compounds of the general formula (XI)

in which A ¹ , A ² , R ¹ , X and Y have the meaning given above and
R represents hydrogen, an alkali metal or alkaline earth metal equivalent (preferably a sodium or potassium), or alkyl (preferably C ₁ -C ₄ alkyl, especially methyl or ethyl),
with (thi) oxo compounds of the general formula (III)

in which
Q and R ^{2 have} the meaning given above and
Q ^{1 represents} halogen, alkoxy, alkylthio, aryloxy or arylthio, preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio, phenyloxy or phenylthio,
- or, if appropriate, with corresponding iso (thio) cyanates -
optionally in the presence of one or more reaction auxiliaries, such as. As potassium carbonate or triethylamine, and optionally in the presence of one or more diluents, such as. B. acetonitrile or N, N-dimethyl-formamide, at temperatures between 0 ° C and 100 ° C.

The process (b) according to the invention for the preparation of compounds of General formula (I) compounds to be used as starting materials are generally defined by the formula (V). In the general formula (V), Z preferably the meaning already mentioned above in connection with the Be description of the compounds of the general formula (I) according to the invention as be preferred, particularly preferred, very particularly preferred or most preferred has been specified for Z.

The starting materials of the general formula (V) are known organic synthesis chemicals.

Formula (Ia) provides a general definition of the substituted benzoyl ketones to be used as starting materials in process (c) for the preparation of compounds of the general formula (I). In the general formula (Ia) A ¹ , A ² , Q, R ¹ , R ² , R ¹⁰ , X and Y preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred, very particularly preferred or most preferred for A ¹ , A ² , Q, R ¹ , R ² , R ¹⁰ , X and Y have been given.

The starting materials of the general formula (Ia) are also counter as new substances stood the present application; they can according to the Ver drive (a) or (b).

Formula (VI) provides a general definition of the aryl ketones to be used as starting materials in process (d) according to the invention for the preparation of compounds of the general formula (I). In the general formula (VI) A ¹ , A ² , Q, R ¹ , X, Y and Z preferably have those meanings which are already preferred above in connection with the description of the compounds of the general formula (I) according to the invention, particularly preferred, very particularly preferred or most preferred for A ¹ , A ² , Q, R ¹ , X, Y and Z; Q ² preferably represents fluorine, chlorine, bromine, C ₁ -C ₃ alkoxy, C ₁ -C ₃ alkylthio, phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy or phenoxy.

The starting materials of the formula (VI) can be known to those skilled in the art Process are made.

Formula (VII) provides a general definition of the compounds to be used further as starting materials in process (d) according to the invention for the preparation of compounds of the general formula (I). In the general formula (VII), R ² preferably has the meaning which has already been given above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most preferred for R ² .

The starting materials of the general formula (VII) are known organic Links.

Formula (X) provides a general definition of the iso (thio) cyanates to be used as starting materials in process (α) for the preparation of compounds of the general formula (IV). In the general formula (X), A ¹ , A ² , Q, X and Y preferably have the meaning which has already been mentioned above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most preferred for A ¹ , A ² , Q, X and Y has been specified.

The starting materials of the general formula (X) are known to the person skilled in the art Process available.  

Formula (XI) provides a general definition of the amino compounds to be used as starting materials in process (β) according to the invention for the preparation of compounds of the general formula (IV). In the general formula (XI), A ¹ , A ² , R ¹ , X and Y preferably have the meaning which has already been mentioned above in connection with the description of the general formula (I) as preferred, particularly preferred, very particularly preferred or most has preferably been given for A ¹ , A ² , R ¹ , X and Y.

The starting materials of the general formula (XI) are according to the person skilled in the art known methods can be produced.

The processes (a), (b), (c) and (d) according to the invention are preferably carried out under Performed using one or more reaction aids. As a reaction tools for processes (a), (b), (c) and (d) according to the invention come in all mean the usual inorganic or organic bases or acid acceptors into consideration. These preferably include alkali metal or alkaline earth metal, acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, Sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, Sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium, methoxide, ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t- butoxide; also basic organic nitrogen compounds, such as such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropyl amine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4- Methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5- Ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl piperidine, N-methyl morpholine, N-ethyl morpholine, 1,4-diazabicyclo [2.2.2] octane (DABCO), 1,5-diazabicyclo [4.3.0] -non-5-ene (DBN), or 1,8-diazabicyclo [5.4.0] - undec-7-en (DBU).  

As further reaction aids for processes (a), (b), (c) according to the invention and (d) phase transfer catalysts are also suitable. As examples of such catalysts are mentioned:

Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, Hexadecyl-trimethylammonium chloride, hexadecyl-trimethylammonium bromide, Benzyl trimethyl ammonium chloride, benzyl triethyl ammonium chloride, benzyl tri methylammonium hydroxide, benzyl triethylammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl hexadecylphosphonium bromide, Butyl triphenylphosphonium chloride, ethyl trioctylphosphonium bromide, tetra phenylphosphonium bromide.

Process (b) according to the invention for the preparation of the new substituted aryl ketones of the general formula (I) is optionally using a De hydrating agent performed. The usual bindings occur here chemicals suitable for water.

Examples of this are dicyclohexylcarbodiimide, carbonyl-bis-imidazole and Called propanephosphonic anhydride.

Dicyclohexylcarbodiimide are particularly suitable dehydrating agents and called propanephosphonic anhydride.

The processes according to the invention for the preparation of the compounds of general My formula (I) are preferably made using diluents carried out. As a diluent for carrying out the inventive In addition to water, processes (a), (b), (c) and (d) primarily involve inert organic ones Solvent. These include in particular aliphatic, alicyclic  or aromatic, optionally halogenated hydrocarbons, such as as petrol, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, Hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ether like Diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol di methyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-Di methylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl pyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as Methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol mono ethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the inventive Processes (a), (b), (c) and (d) can be varied over a wide range. Generally I think one works at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The processes according to the invention are generally carried out under normal pressure guided. However, it is also possible to use the method according to the invention high or reduced pressure - generally between 0.1 bar and 10 bar - perform.

To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The Reaction is generally carried out in a suitable diluent were carried out a reaction auxiliary and the reaction mixture is in space agitated several hours at the required temperature. The on work is carried out according to customary methods (cf. games).  

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used. The active compounds according to the invention can, for. B. in the following plants be used:

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocot cultures of the genera: Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.  

However, the use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the con center for total weed control, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the fiction active agents for weed control in permanent crops, e.g. B. Forst, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, Cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture areas and for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicidal activity solvency and a wide range of effects when used on and on the floor aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocot and di cotyledon cultures, both pre-emergence and post-emergence.

The active compounds according to the invention can be used in certain concentrations or Application rates also to control animal pests and fungal or bacterial plant diseases can be used. You let yourself be given if also as intermediates or precursors for the synthesis of other active ingredients put.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including natural cultivated plants). Cultivated plants can be plants that are caused by conventional breeding and optimization methods or by biotechnological  and obtained genetic engineering methods or combinations of these methods can be, including the transgenic plants and including by Plant variety rights of protectable or non-protectable plant varieties. Under Plant parts are said to be all above-ground and underground parts and organs of the Plants such as sprout, leaf, flower and root are understood to be exemplary Leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well Roots, tubers and rhizomes are listed. One of the plant parts also crops and vegetative and generative propagation material, for example wise cuttings, tubers, rhizomes, offshoots and seeds.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, be wild coming plants (weeds, harmful plants) and / or by conventional biological breeding methods, such as B. crossing or protoplast fusion, obtained Plant types and plant varieties (crops) and their parts treated. In a further preferred embodiment, transgenic plants and Plant varieties by genetic engineering methods, where appropriate in Kombina tion using conventional methods (Genetically Modified Organisms) and their parts treated. The term "parts" or "parts of Plants "or" parts of plants "was explained above.

Plant varieties are cultivated plants with certain properties ("Traits"), both by conventional breeding, by mutagenesis or by recombinant DNA techniques have been obtained. This can be varieties, organic and Be genotypes.

Regarding the transgenic (genetically engineered) to be treated according to the invention Plants or plant varieties include all plants that are genetically engineered Modification genetic material received, which these plants in particular gives some valuable properties ("traits"). Examples of such Eigen are better plant growth, increased tolerance to high or  low temperatures, increased tolerance to drought or water salt or soil salt content, increased flowering performance, easier harvesting, acceleration the ripeness, higher crop yields, higher quality and / or higher nutritional value of the Harvest products, higher shelf life and / or workability of the harvest products. Further and particularly highlighted examples of such properties are one increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants to certain herbicidal active ingredients. As Examples of transgenic plants are the important crops such as cereals (including rice), corn, soybeans, potatoes, cotton, beets, rape, cultivated grass such as golf and ornamental turf, fruit plants (with the fruits apples, pears, citrus fruits and grapes) and plantation crops such as olive and rubber trees mentioned, whereby cereals (including rice), corn, soybeans, potatoes, cotton, beets and rapeseed are highlighted. As properties ("traits") the increased defense of plants against insects by in plant-derived toxins, especially those caused by the genetic Material from Bacillus thuringiensis (e.g. through the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF as well their combinations) are generated in the plants (hereinafter "Bt plants"). The traits that are particularly emphasized are the elevated ones Defense of plants against fungi, bacteria and viruses by systemic Acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. As properties ("traits") the increased tolerance of the plants are particularly emphasized against certain herbicidal active substances and classes of active substances such as glyphosate or glufosinate / phosphinotricin (e.g. "PAT" gene), ALS inhibitors such as Imidazolinones, sulfonylureas and other PPO inhibitors (e.g. plants with Acuron genes), 4-HPD inhibitors such as isoxazoles (e.g. isoxaflutole), ACCase- Inhibitors such as Sethoxydim, as well as Bromoxynil.  

The genes conferring the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. As Examples of "Bt plants" are maize, cotton, soybean and Called potato varieties, which are sold under the trade names YIELD GARD® (e.g. Maize, cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard® (Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are corn varieties, cotton varieties, Soybeans, cereals including rice, beet and rapeseed named under the trade names Roundup Ready® (tolerance against Glyphosate e.g. B. corn, cotton, soybean, beet, rapeseed), Liberty Link® (tolerance against glufosinates, e.g. Rape, maize, beet), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas e.g. maize). As Herbicide-resistant (conventionally grown to herbicide tolerance) plants also the varieties marketed under the name Clearfield © (e.g. maize, rice) mentioned.

Of course, these statements also apply to future developed or future plant varieties with these or future ent developed genetic traits.

Depending on the plant species or plant varieties, their location and growth Conditions (soils, climate, growing season, nutrition) can be determined by the Treatment according to the invention also occurs via additive ("synergistic") effects. For example, reduced application rates and / or extensions of the Spectrum of activity and / or an enhancement of the effect of the invention usable substances and agents - also in combination with other agrochemicals Active ingredients -, better plant growth of crops, increased tolerance of Crops against high or low temperatures, increased tolerance of the Crops against drought or against water salt or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher  Shelf life and / or workability of the harvested products possible via the effects that are actually to be expected.

The plants listed can be particularly advantageous according to the invention with the Compounds of the general formula (I) or the active ingredient according to the invention mixtures are treated, in addition to the good control of the Weed plants have the above synergistic effects with the above plants or plant varieties. The active ingredients or Mixtures of the preferred ranges given above also apply to the treatment of these plants. Plant treatment with the in the This text specifically listed compounds or mixtures.

The treatment according to the invention of the plants and parts of plants with the active ingredients substances takes place directly or by influencing their surroundings, living space or Storage room according to the usual treatment methods, e.g. B. by diving, spraying, Evaporation, atomization, scattering, spreading and with propagation material, especially in the case of seeds, still by single or multi-layer coating.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated nated natural and synthetic substances as well as very fine encapsulation in polymers Substances.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-producing Means.  

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic emuls gators, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite and Methylcellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho lipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.  

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides and / or with substances which Improve crop tolerance ("safeners") for weed control ver can be used, whereby ready formulations or tank mixes are possible. It So mixtures with weed control agents are also possible, which a or contain several known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Amitrole, Anilofos, Asulam, Atrazines, azafenidin, azimsulfuron, beflubutamide, benazolin (-ethyl), benfuresate, Bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromacil, Bromo butide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butenachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone (-ethyl), Chloromethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chloronitrofen, Chlorsulfuron, Chlorthiamid, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulf uron, Clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Cloransulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, Dialates, dicamba, dichlobenil, dichloroprop (-P), diclofop (-methyl), diclosulam, Diethatyl (-ethyl), difenopentene (-ethyl), difenzoquat, diflufenican, diflufenzopyr, Dikegulac (-sodium), Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Di  methenamid (-P), dimexyflam, dinitramine, diphenamide, diquat (-dibromide), di thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulf uron (-methyl), ethiozine, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, Fenoxaprop (-P-ethyl), fentrazamide, flamprop (-M-isopropyl, -M-methyl), flaza sulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flu chloralin, flufenacet, flumetsulam, flumiclorac (-pentyl), flumioxazin, flumi propyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flu propacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxy pyr (-butoxypropyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fome safen, foramsulfuron, glufosinate (-ammonium), glyphosate (-ammonium, -iso propylammonium), halosafen, halosulfuron (-methyl), haloxyfop (-ethoxyethyl, -P- methyl), hexazinones, imazamethabenz (methyl), imazamethapyr, imazamox, Imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxa difen (-ethyl), isoxaflutole, isoxapyrifop, ketospiradox, lactofen, lenacil, linuron, MCPA, Mecoprop (-P), Mefenacet, Mesotrione, Metamitron, Metazachlor, Metha benzthiazuron, methyldymron, metobenzuron, metobromuron, (S-) metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Para quat, pelargonic acid, pendimethalin, pendralin, pentoxazone, pethoxamide, phenmedi pham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), profluazole, Profoxydim, Prometryri, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen (- ethyl), pyrazogyl, pyrazolates, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, Pyributicarb, Pyridafol, Pyridate, Pyridatol, Pyriftalid, Pyriminobac (-methyl), Pyri thiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl, -P- tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, Sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxy dim, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thidiazimin, thifensulf uron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallates, triasulfuron, tri  benuron (-methyl), triclopyr, tridiphane, trifloxysulfuron, trifluralin, triflusulf uron (methyl), tritosulfuron.

Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA- 24, dichlormid, dymron, fenclorim, fenchlorazole (-ethyl), flurazole, fluxofenim, Furilazoles, Isoxadifen (-ethyl), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG- 191, Oxabetrinil, PPG-1292, R-29148.

Also a mixture with other known active ingredients, such as fungicides, insects ziden, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

The amount of active ingredient used can vary over a wide range. she depends essentially on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare of soil area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.  

Preparation Examples

example 1

(Method (a))

To a suspension of 1.0 g (2.9 mmol) [3- (2-aminoethoxy) -2,4-dichlorophenyl] - (1-ethyl-5-hydroxy-1H-pyrazol-4-yl) methanone and 0.8 g (5.8 mmol) of potassium carbonate in 6 ml of acetonitrile, 0.28 g (3.6 mmol) of acetyl chloride are added and the mixture is stirred Reaction mixture for 24 hours at room temperature (approx. 20 ° C). After that it will Solvent removed under reduced pressure and the residue in a little Water dissolved. The aqueous solution is washed with dichloromethane closing with conc. Acidified hydrochloric acid and extracted with ethyl acetate. The organic phase is ge with saturated aqueous sodium chloride solution wash, dry over sodium sulfate and filter. The solution becomes from the filtrate medium carefully distilled off under reduced pressure.

0.8 g (71.5% of theory) of N- (2- {2,6-dichloro-3 - [(1-ethyl-5-hydroxy-1H-pyrazol-4-yl) carbonyl] - phenoxy} ethyl) acetamide (Example I-2-1) as an orange-yellow, glassy solid.
Log P = 1.41.

Example 2

(Method (a))

To a suspension of 0.5 g (1.45 mmol) [3- (2-amino-ethoxy) -2,4-dichlor phenyl] - (1-ethyl-5-hydroxy-1H-pyrazol-4-yl) -methanone in 10 ml of methanol are added 0.24 g (3.3 mmol) of methyl mustard oil (methyl isothiocyanate) and heated the reaction mix 24 hours under reflux to boiling. After adding water and Ethyl acetate, the organic phase is separated off with saturated aqueous Washed sodium chloride solution, dried over sodium sulfate and filtered. from Filtrate, the solvent is carefully distilled off under reduced pressure.

0.55 g (91% of theory) of N- (2- {2,6-dichloro-3 - [(1-ethyl-5-hydroxy-1H pyrazol-4-yl) carbonyl] phenoxy} - is obtained. ethyl) -N'-methyl-thiourea (Example I-2-2) as an orange-yellow viscous oil.
Log P = 1.60.

Example 3

(Method (b))

0.7 g (6.25 mmol) of 1,3-cyclohexanedione and 2.0 g (6.25 mmol) of N- (3-carboxy-2,6-dichlorobenzyl) -N'-isopropyl-thiourea. you the mixture is mixed with 1.5 g (7.25 mmol) of dicyclohexylcarbodiimide and stirred 15 Hours at room temperature (approx. 20 ° C). Then 0.7 g (7 mmol) of triethyl amine and 0.7 g (8 mmol) of 2-hydroxy-2-methyl-propionitrile and the Mixture is stirred for a further 15 hours at room temperature. Then at 50 ml of aqueous 1M potassium carbonate solution stirred, suction filtered and the filtrate with salt acidified to pH 4. It is extracted 3 times with 30 mL dichloromethane, dries the combined organic phases with magnesium sulfate and filtered. Then the solvent is removed under reduced pressure.

1.1 g (30% of theory) of N- (3- (cyclohex-1-en-2-ol-6-one-1-ylcarbonyl) -2,4-dichlorobenzyl-N'-isopropyl-thiourea (Example I -2-3) as an oily residue
LogP = 2.74.

Example 4

subsequent reaction

To a solution of 0.193 g (0.5 mmol) of N- (2- {2,6-dichloro-3 - [(1-ethyl-5-hydroxy- 1H-pyrazol-4-yl) carbonyl] phenoxy} ethyl) acetamide in 6 ml of toluene are added 0.25 g (1.0 mmol) of I-bromo-4- (bromomethyl) benzene and 0.15 g of 1,8-diazabicyclo- [5.4.0] -undec-7-ene (DBU) and the reaction mixture is heated under reflux for 9 hours flow to boiling. The supernatant toluene phase is decanted off and the ver remaining oily residue by column chromatography with dichloromethane / methanol (9: 1) separated as eluent.

0.12 g (43% of theory) of N- {2- [3 - ({5 - [(4-bromo-benzyl) -oxy] -1-ethyl-1H-pyrazol-4-yl} -carbonyl is obtained ) -2,6-dichlorophenoxy] ethyl} acetamide (Example I-2-4) as a yellow viscous oil.
Log P = 2.06.

Analogously to Examples 1 to 4 and in accordance with the general description of the production processes according to the invention, the compounds of the general formula (I) - or of the formulas (I-1) to (I-3) or of the formulas (I-1) or of the formulas (I-2A) to (I-2D).

Table 1

Examples of the compounds of the formula (I-2)

Table 2

Examples of the compounds of formula (I-3)

The logP values specified in the tables were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromato graphy) on a phase inversion column (C 18). Temperature: 43 ° C.

• a) eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - ent Talking measurement results are marked in Table 1 with a).
• b) Eluents for determination in the neutral range: 0.01 molar aqueous Phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% Acetonitrile - corresponding measurement results are marked in Table 1 with b).

The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the Retention times through linear interpolation between two consecutive Alkanones).

The lambda max values were determined using the UV spectra from 200 nm to 400 nm the maxima of the chromatographic signals determined.  

Starting materials of formula (II)

Example (II-1)

step 1

To a solution of 10.0 g (42.5 mmol) of 2,4-dichloro-3-hydroxy-benzoic acid ethyl ester in 100 ml of acetonitrile, 11.7 g (85.1 mmol) of potassium carbonate and after 15 min 11.0 g (46.9 mmol) of 2-chloroethanol tosylate. The reaction mixture is stirred for 19 hours at 70 ° C, concentrated after cooling in vacuo and 50 ml of water and 50 ml of dichloromethane were added to the residue. The organic phase is separated off with water and saturated aqueous sodium washed chloride solution, dried over sodium sulfate and filtered. From the filtrate the solvent is carefully distilled off under reduced pressure.

12.1 g (95% of theory) of 2,4-dichloro-3- (2-chloro-ethoxy) -benzoic acid ethyl ester are obtained as an oil.
Log P = 3.76

Level 2

To a solution of 10.0 g (33.6 mmol) of 2,4-dichloro-3- (2-chloroethoxy) benzo Acid ethyl ester in 70 ml of ethanol gives a solution of 2.2 g (55.0 mmol) Sodium hydroxide in 40 ml of water. The reaction mixture is stirred for 90 minutes Room temperature (approx. 20 ° C) and largely removes the ethanol by evaporation in a vacuum. The residue is concentrated. Hydrochloric acid to pH 1 and with Extracted ethyl acetate. The organic phase is separated off with saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The solvent is carefully removed from the filtrate under reduced pressure distilled.

9.0 g (99% of theory) of 2,4-dichloro-3- (2-chloroethoxy) benzoic acid are obtained as a white solid.
Log P = 2.31

level 3

A solution of 8.5 g (31.5 mmol) of 2,4-dichloro-3- (2-chloroethoxy) benzoic acid in 12 ml of thionyl chloride is heated to 60 ° C for one hour. After gas has ended  development, the excess thionyl chloride is removed under reduced pressure removed.

9.0 g (99% of theory) of 2,4-dichloro-3- (2-chloro ethoxy) benzoyl chloride.

Level 4

To a solution of 3.5 g (31.3 mmol) of 1-ethyl-5-hydroxy-1H-pyrazole in 200 ml Dichloromethane is added in succession to 9.5 g (94 mmol) of triethylamine, 9 g (31.3 mmol) 2,4-dichloro-3- (2-chloroethoxy) benzoic acid chloride and 5 drops of N, N- Dimethyl formamide. The reaction mixture is stirred at room for 21 hours temperature (approx. 20 ° C), then washed with 2 N hydrochloric acid and saturated aqueous Sodium chlorine solution, dries over sodium sulfate and filtered. Removed from the filtrate the solvent under reduced pressure.

The oily residue is dissolved in 200 ml of acetonitrile, with 17 g (168 mmol) of triethyl amine and 3.26 g (38 mmol) of 2-hydroxy-2-methyl-propionitrile and others Stirred for 20 hours at room temperature. The solvent then becomes largely removed under reduced pressure and the oily residue in 100 ml dichlor methane added. The organic phase is with 2N hydrochloric acid and with ge saturated aqueous sodium chloride solution, dried over sodium sulfate and filtered. The filtrate is freed from the solvent under reduced pressure.

11.1 g (98% of theory) [2,4-dichloro-3- (2-chloroethoxy) phenyl] - (1-ethyl-5-hydroxy-1H-pyrazol-4-yl) - methanone as an orange-yellow, crystalline solid.
Log P = 2.73.

Level 5

A solution of 8.0 g (22 mmol) of [2,4-dichloro-3- (2-chloroethoxy) phenyl] - (1-ethyl- 5-hydroxy-1H-pyrazol-4-yl) methanone in 150 ml of tetrahydrofuran and 200 ml Ammonia is heated to 90 ° C in an autoclave for 6.5 hours. That about The ammonia that is deposited is largely evaporated, the product that separates out separated by filtration and dried under reduced pressure.

4.3 g (57% of theory) of [3- (2-aminoethoxy) -2,4-dichlorophenyl] - (1-ethyl-5-hydroxy-1H-pyrazol-4-yl) - methanone as a light yellow, crystalline solid.
Log P = 0.72.

Analogously to Example (II-1), for example the compounds of the general formula (I1I) listed in Table 3 below can also be prepared.

Table 3

Examples of the compounds of the formula (II)

Starting materials of formula (IV)

Example (IV-1)

step 1

In 60 ml of acetonitrile, 15 g (59 mmol) of 2,4- Dichloro-3-bromomethyl-benzoic acid methyl ester and then 7.5 g (77 mmol) Potassium thiocyanate entered. After slowly heating to reflux, the Reaction mixture stirred at this temperature under reflux for 20 hours. To after cooling to room temperature, the solvent is removed in vacuo and the residue was stirred with 70 ml of diethyl ether. You suck off the unsolved, removes the solvent in vacuo and distills under reduced pressure.

2.7 g (17% of theory) of 2,4-dichloro-3-isocyanatomethylbenzoic acid are obtained methyl ester as an oil, which is further reacted without further purification.

Level 2

5.6 g of crude 2,4-dichloro-3-isocyanatomethyl-benzoic acid methyl ester are added in 20 ml of ethanol were dissolved and 1.2 g (20 mmol) of 2-propanamine were added. One heats up the mixture boils for an hour, the amount of solvent is reduced to a third and sucks off.

1.7 g (9% based on 2,4-dichloro-3-methyl-benzoic acid methyl ester) of 2,4-dichloro-3 - [[[(isopropylamino) thioxomethyl] amino] methyl] benzoic acid methyl ester are obtained as Solid (MS: M ⁺ = 355.2 Cl according to the isotope pattern).

level 3

5 g (15 mmol) of N- (3-methoxycarbonyl-2,6-dichlorobenzyl) -N'-isopropyl-thiourea fabric are dissolved in 30 ml of methanol and with 10 ml (50 mmol) of a 30% Solution of sodium methoxide in methanol added. Over 30 minutes 50 ml of water are added dropwise, whereupon the mixture is kept at 60 ° C. for 2 hours. After neutralization with 2N hydrochloric acid, the product is filtered off with suction and dried.

4.4 g (91% of theory) of 2,4-dichloro-3 - [[[(isopropylamino) thioxo are obtained methyl] -amino] -methyl] -benzoic acid as a solid with a melting point <220 ° C.

Analogously to Example (IV-1), for example, the compounds of the general formula (IVa) listed in Table 4 below can also be prepared.

Table 4

Examples of the compounds of the formula (IVa)

applications Example A Pre-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil. After 24 hours the soil is sprayed with the active ingredient preparation so that the desired one Active ingredient quantity is applied per unit area. The drug concentration in the spray liquor is chosen so that the ge in 1000 liters of water per hectare desired amount of active ingredient is applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control)
100% = total annihilation

In this test, for example, the compounds according to the preparation example show (I-2-1), (I-2-3), (I-2-5) and (I-2-6) with partially good tolerance to Cultivated plants, such as. B. corn, soy and wheat, strong action against weeds.  

Example B Post-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5- 15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:
0% = no effect (like untreated control)
100% = total annihilation

In this test, for example, the compounds according to the preparation example show (I-2-1), (I-2-3), (I-2-4), (I-2-5), (I-2-6), (I-2-7) and (I -2-8) with partly good ver inertness to crops, such as. B. corn, rapeseed and wheat, strong Effect against weeds.

Claims (14)

1. Compounds of formula (I)
in which
A ^{1 represents} a single bond or O (oxygen),
A ^{2 represents} alkanediyl (alkylene), alkenediyl or alkindiyl,
Q represents O (oxygen) or S (sulfur),
R ^{1 stands} for hydrogen or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, di alkylamino, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, or for the grouping -C (Q) -R ² ,
R ² for hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, or for each optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, di alkylamino, alkoxyamino, N-alkylalkoxyamino, alkylhydrazino, dialkylhydrazino, alkenyl, alkenyloxy , alkenylamino, alkenyloxy amino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyl oxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cyclo alkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, aryl, alkylthio, arylalkylamino, heterocyclyl , Heterocyclyloxy, hetero cyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclyl alkoxy, heterocyclylalkylthio or heterocyclylalkylamino,
X stands for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl,
Y stands for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl, and
Z represents one of the groupings below
in which
m represents the numbers 0 to 6,
R ^{3 represents} hydrogen, halogen or in each case optionally substituted alkyl, alkylthio or aryl, or - if m represents 2 - optionally also together with a second radical R ^{3 represents} oxygen or alkanediyl (alkylene), R ⁴ for hydroxyl, formyloxy, halogen, or for optionally substituted alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylamino carbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxyloxy arylcarbonyloxyalkyl , Arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl,
R ^{5 stands} for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or for optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxycarbonyl or cycloalkyl,
R ^{6 stands} for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl,
R ^{7 represents} hydroxy, formyloxy, or in each case optionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy, alkynyloxy, arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy,
R ^{8 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl,
R ^{9 represents} hydrogen or represents optionally substituted alkyl or cycloalkyl,
R ^{10 represents} hydrogen or represents optionally substituted alkyl or cycloalkyl, and
R ^{11 represents} hydrogen, cyano, carbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl. 2. Compounds of formula (I) according to claim 1, characterized in that
A ^{1 stands} for O (oxygen),
A ^{2 represents} alkanediyl (alkylene), alkenediyl or alkindiyl each having up to 6 carbon atoms,
Q stands for O (oxygen),
R ¹ represents hydrogen, represents in each case optionally cyano-, halogen-, C ₁ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkyl sulfonyl substituted alkyl, alkoxy, Alkylthio, alkylsulfinyl, alkyl sulfonyl or alkylamino each having 1 to 6 carbon atoms in the alkyl groups, for dialkylamino each having 1 to 4 carbon atoms in the alkyl groups, for each alkenyl or alkynyl optionally substituted by cyano or halogen, each having 2 to 6 carbon atoms, for in each case optionally substituted by cyano, halogen or C ₁ -C ₄ -alkyl cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ -halogen alkyl, C ₁ -C ₄ alkoxy or C ₁ -C each having 6 or 10 carbon atoms group ₄ haloalkoxy substituted aryl or arylalkyl in the aryl and optionally 1 to 4 carbon atoms in the alkyl part, or represents the group -C (Q) -R ² ,
R ² for hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, for C ₁ -C ₄ -alkyl-carbonyl, for C ₁ -C ₄ -alkoxy-carbonyl, for each optionally by cyano, halogen, C ₁ -C ₄ Alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylamino, alkoxyamino or alkylhydrazino, each having 1 to 6 carbon atoms in the alkyl groups, for dialkylamino, N-alkylalkoxyamino or dialkyl hydrazino each having 1 to 4 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy or alkynylamino each having 2 to 6 carbon atoms each optionally substituted by halogen cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl group and given by cyano, halogen or C ₁ -C ₄ alkyl optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy or C ₁ -C ₄ alkoxy-carbonyl-substituted aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylamino each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the Alkyl part, or for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ - Alkylthio, C ₁ -C ₄ -haloalkylthio or C ₁ -C ₄ -alkoxy-carbonyl-substituted monocyclic or bicyclic heterocyclyl, hetero cyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy, heteroalkyl-heterocyclo-cyclyl-alkyllylyl-cyclo-alkyl-thio-cyclyl-alkyllyl to 10 carbon atoms and additionally at least one heteroatom selected from the series nitrogen (N) (but not more than 5 N atoms), oxygen (O) (but not more than 2 O atoms), sulfur (S) (but not more than 2 S atoms), SO or SO ₂ and optionally additionally a group selected from oxo (C = O), thioxo (C = S), imino (C = NH), cyanoimino (C = N-CN), nitroimino (C = N-NO ₂ ) contains
X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen-, C ₁ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ -alkyl sulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups,
Y represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen-, C ₁ - C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ -alkyl sulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkyl sulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl each having 1 to 6 carbon atoms in the alkyl groups,
Z represents one of the groupings below,
m represents the numbers 0 to 3,
R ^{3 represents} hydrogen, halogen, each optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl substituted alkyl or alkylthio each with 1 to 6 carbon atoms, or for phenyl, or - if m is 2 - optionally together with a second radical R ^{3 is} oxygen or alkanediyl (alkylene) with 3 to 5 carbon atoms,
R ⁴ for hydroxy, formyloxy, halogen, for alkoxy optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl , Alkylthio, alkyl sulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy each having 1 to 6 carbon atoms, for each optionally substituted by halogen substituted alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, for each optionally using nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ haloalkylsulfonyl substituted aryloxy, arylthio, aryl sulfinyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, aryl sulfonyloxy, arylalkoxy, Arylalkylthio, arylalkylsulfinyl or aryl alkylsulfonyl, each with 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part,
R ^{5 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, for each optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ -Alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups or for cycloalkyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkyl having 3 to 6 carbon atoms.
R ^{6 is} hydrogen, alkyl which is optionally substituted by cyano, halogen, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl and has 1 to 6 Carbon atoms, each for alkenyl or alkynyl optionally substituted by cyano or halogen, each having 3 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl, each having 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy , C ₁ -C ₄ alkylthio, C ₁ -C ₄ halo alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ haloalkylsulfonyl substituted Aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and given optionally 1 to 4 carbon atoms in the alkyl part,
R ⁷ for hydroxy, formyloxy, for alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano or halogen Alkenyloxy or alkynyloxy each having 3 to 6 carbon atoms, or for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -Halogenalkoxy, C ₁ - C ₄ -alkylthio, C ₁ -C ₄ -haloalkylthio, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ - haloalkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl or C ₁ -C ₄ -haloalkyl sulfonyl-substituted arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulfonyloxy each having 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl part,
R ⁸ for hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkyl thio, alkylsulfinyl or alkylsulfonyl, each with 1 to 6 carbon in each case optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy atoms in the alkyl groups,
R ⁹ represents hydrogen, represents optionally cyano-, halogen or C ₁ -C ₄ - ₄ alkyl substituted cycloalkyl alkoxy substituted alkyl, or represents optionally cyano-, halogen- or C ₁ -C having 3 to 6 carbon atoms,
₄ alkyl substituted cycloalkyl alkoxy substituted alkyl, or represents optionally cyano-, halogen- or C ₁ -C having 3 to 6 carbon atoms, and - R ¹⁰ represents hydrogen, represents optionally cyano-, halogen or C ₁ -C ₄
R ¹¹ for hydrogen, cyano, carbamoyl, halogen, or for alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkyl sulfonyl, each with 1 to 6 carbon atoms in the alkyl groups, optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy stands. 3. Compounds of formula (I) according to claim 1, characterized in that
A ² for methylene (-CH ₂ -), ethane-1,1-diyl (-CH (CH ₃ ) -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -), propane-1 , 1-diyl (-CH (C ₂ H ₅ ) -), propane-1,2-diyl (-CH (CH ₃ ) CH ₂ -), propane-1,3-diyl (-CH ₂ CH ₂ CH ₂ -), butane-1,3-diyl (- CH (CH ₃ ) CH ₂ CH ₂ -), butane-1,4-diyl (-CH ₂ CH ₂ CH ₂ CH ₂ -), ethendiyl, propendiyl, butenediyl, Ethindiyl, propindiyl or butynediyl,
R ¹ for hydrogen, for each optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propyl sulfinyl , Methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i Propoxy, n-, i-, s- or t-butoxy, methyl thio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i Propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, for dimethylamino or diethylamino, for ethenyl optionally substituted by fluorine, chlorine and / or bromine , Propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, for in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or propyl cyclopropyl, cyclobutyl, cyclopentyl, cyclo hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromoxy substituted phenyl, naphthyl, phenylmethyl, phenylethyl, naphthylmethyl or naphthylethyl or for grouping -C (Q) -R ² ,
R ² for hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl , n- or i-Propylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy , Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, Ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, methylhydrazino, ethylhydrazino, n- or i-Propyl hydrazino, n-, i-, s- or t-butylhydrazino, for dimethylamino, diethylamino, N-methyl-methoxyamino, dimethylhydrazino or diethylhydrazino, each optionally substituted by fluorine, chlorine and / or bromine Ethenyl, propenyl, butenyl, Pentenyl, ethynyl, propynyl, butynyl, pentynyl, propenyloxy, butenyloxy, pentenyloxy, propenylthio, butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino, propenyloxyamino, butenyloxyamino, pentenyloxyamino, ethynyl, propynyl, propynyl, pentyloxy, pentyloxy, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino, pentyloxyamino Butynylamino or pentynylamino, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, cyclohexylamino, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or propyl Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropyl methoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexyl-methoxy, Cyclopropylmethylamino, Cyclobuylmethylamino, Cyclo pentylmethylamino or Cyclohexylmethylamino, for each given optionally by methyl, Ethyl, bromine, by Nitro, bromine, nyl, Cyano, nano, by Nitro, bromine, Cyano -Propyl, n-, i-, s - or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, naphthyl , naphthyloxy, Naphtylthio, naphthylamino, phenylmethyl, phenylethyl, phenylmethoxy, phenyl ethoxy, phenylmethylthio, phenylethylthio, phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl, naphthyl, methoxy, naphthylethoxy, naphthylmethylamino or naphthylethyl amino, or represents in each case optionally substituted by nitro, cyano, fluorine, chlorine , Bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio , Methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl-substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino, heterocyclylalkyl, heterocyclylalkoxy or methoxy heterocyclylalkylamino from the series furyl, furyloxy, Furylamino, furylmethyl, furyl, furylmethylamino, thienyl, thienylmethyl, pyrrolidinyl, Pyrrolidinylamino , Oxopyrrolidinyl, Pyrrolyl, Indolyl, Pyrrolylmethyl, Pyrazolyl, Pyrazolyloxy, Pyrazolylamino, Pyrazolylmethyl, Imid azolyl, Imidazolylmethyl, 2-Oxo-1,3-diaza-cyclopentyl, Oxazolyl, Di hydrooxazolyl (Oxazolylolol), Isox (isoxazolidinyl), oxazolyl methyl, thiazolyl, dihydrothiazolyl (thiazolinyl), tetrahydro thiazolyl (thiazolidinyl), thiazolylmethyl, thiazolidinyl, Oxothi azolidinyl, Cyanoiminothiazolidinyl, Oxotriazolinyl, Oxotetrazolinyl, piperidinyl, piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza cyclohexyl, 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cyclohept yl, morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyl oxy, pyridinylamino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl, pyrimidinylmethoxy,
X represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or for each methyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl,
Y for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or for each methyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl,
m represents the numbers 0, 1 or 2,
R ³ for fluorine, chlorine or bromine, each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl thio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, or for phenyl, or - if m is 2 - optionally also together with a second radical R ^{3 is} oxygen, propane-1,3-diyl or butane-1,4-diyl,
R ⁴ for hydroxy, formyloxy, fluorine or chlorine, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyl - or i-Propoxycarbonyloxy, methyl aminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylamino carbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propyl sulfonyloxy, for propenyloxy, butenyloxy, propynyloxy or butynyloxy each optionally substituted by fluorine, chlorine and / or bromine , for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, difluoromethoxy, Trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoro methylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, tri fluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or methylsulfonyl trifluoro substituted phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, Phenylcarbonylalkoxy, phenyl sulfonyloxy, phenylmethoxy, phenylmethylthio , Phenylmethylsulfinyl or phenylmethylsulfonyl,
R ⁵ for hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl , Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or represents in each case cyclopropyl, cyclobutyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl,
R ^{6 represents} hydrogen, for methyl, ethyl substituted in each case by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, n- or i-propyl, n-, i-, s- or t-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by cyano, fluorine, chlorine or bromine, for each optionally by cyano, fluorine, chlorine , Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclo hexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t -Butylthio-methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, T rifluonomethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenyl or phenylmethyl,
R ⁷ for hydroxy, formyloxy, for methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, Methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylamino carbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propylene substituted by cyano, fluorine, chlorine or bromineoxy, if appropriate in each case , Propynyloxy or butynyloxy, or if appropriate by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl enyl methoxy, phenylcarbonyloxy, phenylcarbonylmethoxy or phenyl sulfonyloxy,
R ^{8 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, or methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,
R ^{9 represents} hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, or represents in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
R ^{10 is} hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, or represents in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and
R ^{11 is} hydrogen, cyano, carbamoyl, fluorine, chlorine or bromine, or is methyl, ethyl, n- or i-propyl, n- which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy. , i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methyl sulfonyl or ethylsulfonyl. 4. Compounds of formula (I) according to claim 1, characterized in that
A ^{2 represents} methylene (-CH ₂ -), ethane-1,2-diyl (dimethylene, -CH ₂ CH ₂ -) or propane-1,3-diyl (-CH ₂ CH ₂ CH ₂ -),
R ¹ for hydrogen, for each methyl, ethyl, n- or i-propyl, n- or i-butyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, for dimethylamino, for propenyl, butenyl optionally substituted by fluorine and / or chlorine , Ethynyl, propynyl or butynyl, each for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, optionally substituted by cyano, fluorine, chlorine or methyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine , Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl, phenylmethyl or phenyl ethyl, or for grouping -C (Q) -R ² ,
R ² for hydrogen, amino, hydroxyamino, hydrazino, for where appropriate by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino , Ethylamino, n- or i-propylamino, methoxy amino, ethoxyamino, n- or i-propoxyamino, for dimethylamino, for N-methyl-methoxyamino, for dimethylhydrazino, for in each case optionally substituted by fluorine and / or chlorine, ethenyl, propenyl, Butenyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, for each cyclopropyl, cyclobutyl, cyclylentyl, cyclo butyl substituted by cyano, fluorine, chlorine or methyl Cyclopropylmethy l, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy , Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylamino, phenylmethyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio , Ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted monocyclic or bicyclic heterocyclyl or heterocyclyl alkyl from the series furyl, furylmethyl, thienyl, thienolidomethyl inyl, oxopyrrolidinyl, pyrrolyl, pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, imidazolyl, imidazolylmethyl, 2-oxo-1,3-diaza cyclopentyl, oxazolyl, isoxazolyl, oxazolylmethyl, isoxazolidinyl, thiazolyl, thiazolidyl, piperylidyl, piperylidyl, oxiperidyl, oxiperidyl, piperylidyl, piperylidyl, piperylidyl, piperylidyl, piperidyl, piperidyl, piperidyl, piperidyl diazacyclohexyl, morpholinyl, piperazinyl, pyridinyl, pyridinyl methyl, pyrimidinyl, pyrimidinylmethyl,
X for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinyl methyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy , Trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl,
Y for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methyl sulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, eththio , Ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl,
m represents the numbers 0 or 1,
R ³ for hydrogen, for in each case optionally substituted by fluorine and / or chlorine, methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or for phenyl, or - in the event that m for 2 - optionally also together with a second radical R ^{3 represents} oxygen, propane-1,3-diyl or butane-1,4-diyl,
R ⁴ for hydroxy, for formyloxy, for methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy each optionally substituted by fluorine and / or chlorine , Propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylamino carbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for and / or chlorine-substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, difluoromethoxy or trifluoromethoxy substituted phenyloxy, phenylthio, phenyl sulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonyl methoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenyl methylsulfmyl or phenylmethylsulfonyl,
R ⁵ for hydrogen, cyano, fluorine, chlorine, for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or, in each case optionally substituted by fluorine and / or chlorine i- propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, or each represents cyclopropyl optionally substituted by cyano, fluorine, chlorine or methyl,
R ⁶ for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for in each case optionally by fluorine or Chlorine-substituted propenyl, butenyl, propynyl or butynyl, for each optionally by cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted by fluorine, chlorine or methyl, or for each optionally by fluorine, chlorine, bromine, methyl, ethyl, n- or i- Propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy substituted phenyl or phenylmethyl,
R ⁷ for hydroxy, for formyloxy, for methoxy, ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy , Methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylamino carbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy, for propylene optionally substituted by fluorine and / or chlorine, oxyphenyloxy , Propynyloxy or butynyloxy, or for phenylmethoxy substituted in each case by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy , Phenyl carbonyloxy, phenylcarbonylmethoxy or phenylsulfonyloxy,
R ⁸ for hydrogen, cyano, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy which is optionally substituted by fluorine, chlorine, methoxy or ethoxy , Ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,
R ^{9 represents} hydrogen, each represents methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents cyclopropyl which is optionally substituted by fluorine, chlorine or methyl,
R ^{10 represents} hydrogen, in each case represents methyl, ethyl, n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, or represents cyclopropyl optionally substituted by fluorine, chlorine or methyl, and
R ¹¹ for hydrogen, cyano, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl optionally substituted by fluorine, chlorine, methoxy or ethoxy , Ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl. 5. Compounds of formula (I) according to claim 1, characterized in that
R ^{1 represents} hydrogen, in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, methyl, ethyl, n- or i-propyl, methoxy or ethoxy or for grouping -C (Q) -R ² ,
R ² for hydrogen, amino, hydrazino, for each methyl, ethyl or n- or i-propyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for dimethylamino, for cyclopropyl, cyclobutyl, cyclopentyl, each optionally substituted by fluorine, chlorine or methyl or cyclohexyl, for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl or n- or i-propyl, methoxy, ethoxy or n- or i-propoxy, phenyl, phenylamino, phenylmethyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodi fluoromethyl, fluorodichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, methcarbonylcarbonyl, ethoxycarbonyl, ethoxycarbonyl, ethoxy Furylmethyl, thienyl, thienylmethyl, pyrrolyl or pyrrolylmethyl,
X represents hydrogen, nitro, fluorine, chlorine, bromine, methyl, ethyl or tri fluoromethyl,
Y for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methyl sulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, eththio , Ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl,
R ^{3 represents} hydrogen or methyl or ethyl which is optionally substituted by fluorine and / or chlorine,
R ^{4 represents} hydroxy,
R ^{5 represents} hydrogen, fluorine, chlorine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine,
R ^{6 represents} hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, methoxy or ethoxy,
R ^{7 represents} hydroxy, methoxy or ethoxy optionally substituted by fluorine or chlorine, or phenylmethoxy optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy or ethoxy. 6. A process for the preparation of compounds of formula I according to claim 1, characterized in that

• a) compounds of the general formula (II)
  in which
  A ¹ , A ² , R ¹ , X, Y and Z have the meaning given in claim 1, with compounds of the general formula (III)
  in which
  Q and R ^{2 have} the meaning given in claim 1 and
  Q ^{1 represents} halogen, alkoxy, alkylthio, aryloxy or arylthio,
  - or, if appropriate, with corresponding iso (thio) cyanates -
  if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
  or if you
• b) carboxylic acids of the general formula (IV)
  in which
  A ¹ , A ² , Q, R ¹ , R ² , X and Y have the meaning given in claim 1
  - or reactive derivatives thereof, such as. B. corresponding acid halides, acid cyanides or esters -
  with compounds of the general formula (V)
  HZ (V)
  in which
  Z has the meaning given in claim 1,
  if appropriate in the presence of a dehydrating agent and if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
  or if you
• c) substituted benzoyl ketones of the general formula (Ia)
  in which
  A ¹ , A ² , Q, R ¹ , R ² , R ¹⁰ , X and Y have the meaning given in claim 1,
  with an orthoformic acid ester or with an N, N-dimethylformamide acetal or with a cyanoformic acid ester or with carbon disulfide (carbon disulfide) and an alkylating agent and then with hydroxylamine or an acid adduct thereof
  if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
  or if you
• d) aryl ketones of the general formula (VI)
  in which
  A ¹ , A ² , Q, R ¹ , X, Y and Z have the meaning given in claim 1 and
  Q ^{2 represents} halogen, alkoxy, alkylthio, aryloxy or arylthio,
  - or, if appropriate, corresponding iso (thio) cyanates -
  with compounds of the general formula (VII)
  HR ² (VII)
  in which
  R ^{2 has} the meaning given in claim 1,
  if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
  and optionally following the implementation of processes (a), (b), (c) or (d) on the compounds of the general formula (I) thus obtained, subsequent reactions for conversion into other compounds of the general formula (I) by customary methods performs.

7. Compounds of the formula (II)

• a) compounds of the general formula (II)
  in which
  A ¹ , A ² , R, X, Y and Z have the meaning given in claim 1.

8. A process for the preparation of compounds of the formula (1I), characterized in that compounds of the general formula (VIII)
in which
A ¹ , A ² , X, Y and Z have the meaning given in claim 1 and
X ^{1 represents} halogen,
with ammonia or amino compounds of the general formula (IX)
in which
R ^{1 has} the meaning given in claim 1, if appropriate in the presence of a diluent, if appropriate under elevated pressure at temperatures between 0 ° C. and 100 ° C. 9. Compounds of formula (IV)
in which
A ¹ , A ² , Q, R ¹ , R ² , X and Y have the meaning given in claim 1. 10. A process for the preparation of compounds of formula (IV), characterized in that

• 1. (α) compounds of the general formula (X)
  in which
  A ¹ , A ² , Q, X and Y have the meaning given in claim 1 and
  R represents hydrogen, an alkali metal or alkaline earth metal equivalent or alkyl,
  with compounds of the general formula (VII)
  HR ² (VII)
  in which
  R ^{2 has} the meaning given in claim 1,
  if appropriate in the presence of a diluent at temperatures between 0 ° C. and 100 ° C. and if appropriate subsequently carrying out an ester hydrolysis by customary methods,
  or if you
• 2. (β) compounds of the general formula (XI)
  in which
  A ¹ , A ² , R ¹ , X and Y have the meaning given in claim 1 and R represents hydrogen, an alkali metal or alkaline earth metal equivalent or alkyl,
  with (thi) oxo compounds of the general formula (III) in which
  Q and R ^{2 have} the meaning given in claim 1 and
  Q ^{1 represents} halogen, alkoxy, alkylthio, aryloxy or arylthio,
  - or, if appropriate, with corresponding iso (thio) cyanates -
  if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents at temperatures between 0 ° C. and 100 ° C.

11. Compounds of the formula (Ia)
in which
A ¹ , A ² , Q, R ¹ , R ² , R ¹⁰ , X and Y have the meaning given in claim 1. 12. Herbicidal agents, characterized by the content of at least one Connection according to one of claims 1 to 5 and the usual stretch convey. 13. Use of at least one compound according to one of the claims 1 to 5 or an agent according to claim 12 for combating imm wanted plants. 14. A method for controlling unwanted plants, characterized records that one has at least one connection according to one of the claims 1 to 5 or an agent according to claim 12 on the undesirable plants and / or their living space.